Abstract
Oligo-chitosans were chemically modified with dinitrophenyl groups for selective and rapid adsorption of amitriptyline by forming π-π complexes. 1H-NMR was utilized not only for characterization of modified chitosans but also for monitoring the aromatic-aromatic interaction. The variation in the chemical shift of aromatic protons was followed to monitor the aromatic-aromatic interaction. Upfield shift of aromatic protons of dinitrophenyl groups supports aromatic-aromatic interactions with amitriptyline. Drug uptake test by HPLC reveals that dinitrophenyl chitosan particles (1–2 μm) at 0.4 wt% (w/v) in a saline solution (pH 6.9) adsorb 90% amitriptyline within 30 min.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Bianco A, Chiacchio U, Rescifina A, Romeo G, Uccella N (1997) Biomimetic supramolecular biophenol-carbohydrate and biophenol-protein models by NMR experiments. J. Agric. Food Chem. 45: 4281–4287.
Cubberley MS, Iverson BL (2001) 1H-NMR investigation of solvent effects in aromatic stacking interaction. J. Am. Chem. Soc. 123: 7560–7563.
Domszy JG, Roberts GAF (1985) Reaction of chitosan: 5. The reaction of chitosan with 2,4-dinitrofluorobenzene and determination of the extent of the reaction. Int. J. Biol. Macromol. 7: 45–48.
Funasaki N, Nomura M, Ishikawa S, Neya S (2001) NMR chemical shift references for binding constant determination in aqueous solutions. J. Phys. Chem. 105: 7361–7365.
Hanna MV, Ashhaugh AL (1964) Nuclear magnetic resonance study of molecular complexes of 7,7,8,8-tetracyanoquinodimethane and aromatic donors. J. Phys. Chem. 68: 811–816.
Kubota N, Tatsumoto N, Sano T, Toya K (2000) A simple preparation of half N-acetylated chitosan highly soluble in water and aqueous organic solvents. Carbohydrate Res. 324: 268–274.
Laatikainen R, Ratilainen Jari, Sebastian R, Santa H (1995) NMR study of aromatic-aromatic interactions for benzene and some other fundamental aromatic systems using alignment of aromatics in strong magnetic field. J. Am. Chem. Soc. 117: 11006–11010.
Meyer EA, Castellano RK, Diederich F (2003) Interaction with aromatic rings in chemical and biological recognition. Angew. Chem. Int. Ed. 42: 1210–1250.
Park SH, Kwon OS, Choi, CW, Kim CJ (2000) Glucosaminemeditated detoxification of p-benzoquinone and its removal by chitosan. Biotechnol. Lett. 22: 21–24.
Rashkin ML, Waters ML (2002) Unexpected substituent effects in offset ?-? stacked interaction in water. J. Am. Chem. Soc. 124: 1860–1861.
Sinnokrot MO, Valeev EF, Sherrill CD (2002) Estimates of the ab initio limit for ?-? interactions: the benzene dimmer. J. Am. Chem. Soc. 124: 10887–10893.
Underhill RS, Jovanovic AV, Carino SR, Varshney M, Shah MO, Dennis DM, Moery TE, Duran RS (2002) Oil filled silica nanocapsules for lipophilic drug uptake: implication of drug detoxification therapy. Chem. Mater. 14: 4919–4925.
Zych AJ, Iverson BL (2000) Synthesis and conformational characterization of tethered, self-complexing 1,5-dialkoxynaphthalene/1,4,5,8-naphthalenetetracarboxylic diimide systems. J. Am. Chem. Soc. 122: 8898–8909.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Lee, DW., Baney, R. Detoxification of amitriptyline by oligochitosan derivatives. Biotechnology Letters 26, 713–716 (2004). https://doi.org/10.1023/B:BILE.0000024094.16474.35
Issue Date:
DOI: https://doi.org/10.1023/B:BILE.0000024094.16474.35